Synlett 2006(10): 1453-1466  
DOI: 10.1055/s-2006-941592
ACCOUNT
© Georg Thieme Verlag Stuttgart · New York

Catalytic Applications of Chiral Organoselenium Compounds in Asymmetric Synthesis

Antonio L. Braga*, Diogo S. Lüdtke, Fabrício Vargas, Rodolpho C. Braga
Departamento de Química, Universidade Federal de Santa Maria, 97105-900, Santa Maria, RS, Brazil
Fax: +55(55)32208998; e-Mail: albraga@quimica.ufsm.br;
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Publikationsverlauf

Received 29 November 2005
Publikationsdatum:
12. Juni 2006 (online)

Abstract

Chiral selenium-containing compounds have found growing application in asymmetric catalysis over the past few years. The large majority of these ligands are derived from readily available chiral amino alcohols in a few high-yielding synthetic steps. The advantages of using these compounds are described, ­particularly those regarding ready accessibility, modular nature, formation of strong bonds with soft metals and more rarely with hard ones.
By using an appropriate electrophilic or nucleophilic organoselenium fragment, novel chiral organoselenium catalysts or ligands were designed from chiral aziridines, oxazolines, ferrocenes, etc. High regioselectivity and enantioselectivity were achieved through the four following techniques: the enantioselective copper-catalyzed conjugate addition of organometallic reagents to enones, the diorganozinc addition to aldehydes, palladium-catalyzed enantioselective allylic alkylation and asymmetric hydrosilylation or transfer hydrogenations of ketones.

  • 1 Introduction

  • 2 Chiral Organoselenium Compounds as Catalysts for ­Enantioselective Synthesis

  • 2.1 Enantioselective Hydrosilylation of Ketones

  • 2.2 Enantioselective Addition of Diorganozinc Reagents to ­Aldehydes

  • 2.3 Enantioselective Conjugate Additions to Enones

  • 2.4 Palladium-Catalyzed Asymmetric Allylic Alkylations

  • 3 Summary and Outlook